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The pH of a salt solution is determined by its component anions and cations. Salts that contain pH-neutral anions and the hydronium ion-producing cations form a solution with a pH less than 7. For example, in ammonium nitrate (NH4NO3) solution, NO3− ions do not react with water whereas NH4+ ions produce the hydronium ions resulting in the acidic solution.  In contrast, salts that contain pH-neutral cations and the hydroxide ion-producing anions form a solution with a pH greater than...
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Acids and bases play several important roles in biology. The pH of a biological system can significantly impact the function of biological molecules, including enzymes, proteins, and nucleic acids. For example, enzymes have optimal pH ranges for their activity, and changes in pH can denature or alter their structure, affecting their function. Acids and bases also play a crucial role in cellular signaling and communication. The pH of the extracellular fluid around cells can influence the...
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Integrative Salt Selection and Formulation Optimization: Perspectives of Disproportionation and Microenvironmental pH

Shikhar Mohan1, Yi Li1, Kevin Chu2

  • 1Gilead Sciences, Inc., Foster City, California 94404, United States.

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|April 24, 2024
PubMed
Summary
This summary is machine-generated.

This study introduces fumaric acid as a novel pH modifier to prevent drug salt disproportionation in tablet formulations. This approach enhances drug solubility and bioavailability by stabilizing the formulation during absorption.

Keywords:
Raman spectroscopyX-ray diffractionchemometricsformulationmicroenvironmental pHpH modifiersalt disproportionationspring-and-parachute

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Area of Science:

  • Pharmaceutical Sciences
  • Drug Delivery
  • Physical Chemistry

Background:

  • Drug bioavailability is often limited by poor solubility, necessitating solubility enhancement strategies.
  • Drug salt disproportionation can lead to a significant drop in solubility during absorption, impacting bioavailability.
  • Limited salt and cocrystal options exist for certain drug molecules with bioavailability challenges.

Purpose of the Study:

  • To investigate the use of a pH modifier as a disproportionation retardant in tablet formulations.
  • To enhance the solubility and bioavailability of a drug molecule facing disproportionation risks.
  • To develop an innovative risk-mitigating strategy for salt disproportionation in pharmaceutical formulations.

Main Methods:

  • Utilized Raman spectroscopy with chemometrics and quantitative X-ray diffraction for stress testing.
  • Investigated disproportionation phenomena under controlled stress conditions.
  • Employed fumaric acid as a microenvironmental pH modulator in tablet formulations.

Main Results:

  • Fumaric acid demonstrated a synergistic advantage in preventing disproportionation for both high-risk (HCl) and moderate-risk (maleate) scenarios.
  • The interaction of fumaric acid with the freebase released during disproportionation formed a more soluble hemifumarate species.
  • This hemifumarate formation helped maintain elevated drug solubility, mitigating the solubility drop during the 'parachute' phase.

Conclusions:

  • A novel utilization of a pH modifier (fumaric acid) as a disproportionation retardant in tablet formulations was reported.
  • This approach effectively mediates the solubility drop during drug absorption, offering a potential risk-mitigating strategy for salt disproportionation.
  • The findings demonstrate an innovative technique using compendial excipients to improve drug solubility and bioavailability.